It’s like John Lennon said: life is what happens to you while you’re busy making other plans. For Steve Chan of Carlton North cafe-wine bar Sleepy’s, the plan was to go to university and find a career calling. It didn’t work out that way.

“I chopped and changed degrees because I have the privileged mindset of, ‘Oh, I’ll find something that I like,’” Chan tells Broadsheet. “So I did that for four years, but in those four years I was like, ‘I want to learn how to make coffee – I want to learn a skill before I commit to being corporate.’” A part-time gig at Cofi House cafe in Sydney was enough to convince Chan where his true passions lay. “On the till and doing the dishes, I was like, ‘I’m getting so much joy and happiness, oddly, from this. I’m gonna do this forever.’”

Chan, a Sydneysider, fell in love with Melbourne’s coffee culture after a weekend research trip that involved going to 10 cafes each day. Eventually he chose the city as a home for his own space. Rather than the standard cafe model, though, Chan preferred the versatility of all-day service. “Back in the day, one of my favourite places was Sun Moth Canteen in the city,” he says.

Like the sadly departed Sun Moth, Sleepy’s does cafe fare during daylight hours before slipping into wine-bar mode at night. Whatever time you head in, you’ll find a menu shaped by Chan’s Chinese-Australian heritage, plus his figuring-it-out-as-I-go approach to cooking. To manage this style, which he’s described as “controlled chaos”, he relies on a few key tools from Square. “We can change buttons around, we can add things last minute – it’s super flexible to our needs.”

While working in the kitchen was never in Chan’s original plans, his inventive, personal menu ended up fuelling much of Sleepy’s popularity. “The beauty of it is, because I’ve never worked in a kitchen before, I don’t know what people like to eat, really,” Chan says. But the success of his dishes says otherwise.

In the morning, favourites include the breakfast dumplings (chopped up bacon and scrambled eggs in a fried dumpling wrapper) and the mee goreng-stuffed toastie. The congee with chilli oil and choose-your-own toppings is probably Sleepy’s signature dish, and it’s a chance for Chan to share a little piece of his own history. “Congee was always a thing for me growing up,” he says. “It’s been nice feeding everyone bits of my culture, and I love the fact that congee can be super accessible – it can be gluten-free or vegan, but also meaty if you want.”

Come evenings – which is when you’re most likely to see Chan man the pans these days – the menu switches to nostalgic, wine-friendly dishes. A Chinese take on an Italian-American classic, for instance, hits some important notes for Chan. “Our noodles-and-meatballs dish is ripped literally straight off my grandma’s recipe for the lion’s head meatball,” he says. “I shrunk it down to a meatball size and then made other things around it to give it more like a spaghetti-and-meatballs vibe.”

Sleepy’s popularity owes much to Chan’s personal generosity and irreverent creativity, though he admits to more than a few bouts of imposter syndrome along the way. He’s also added a near-endless stream of pop-ups to the mix. Although it sounds overwhelming, Chan says he’s able to integrate all these activations onto the one platform with Square, helping him keep up with the public’s growing love for the little Carlton North diner.

“We’re always very pop-up heavy. We love celebrating the community and all that stuff, but because of that it’s also super chaotic, and Square lets us be that chaos,” he says. “It can be as simple or as complicated as we need, at least for a small venue.”

This article is produced by Broadsheet in partnership with Square.